Meet Annie Middleton

Annie Middleton didn’t set out to start a hosting company — she just wanted websites to stay online.

After years of watching servers go down, backups not exist, and entire weekends disappear into emergency fixes, she hit a breaking point. Reliability mattered to her. Clients mattered. And “we’ll deal with it later” wasn’t good enough. So she built something better.

In this interview, Annie shares how Nine Planets grew out of a very real frustration with broken systems, why staying busy is often the enemy of real progress, and how raising prices (yes, really) ended up adding meaningful, recurring revenue without blowing everything up. There’s a lot here for anyone who cares about doing solid work, protecting their time, and building infrastructure that doesn’t constantly need babysitting.

If you’ve ever found yourself fixing the same preventable problem over and over and thinking, there has to be a better way, you’re going to enjoy Annie’s perspective.

What got you into WordPress and how long have you been using it?

I first got into WordPress in 2005 when I was looking for a way to build websites quickly and affordably for small businesses. Before that, I was creating fully custom websites, which worked well but was time-consuming and expensive for many organizations.

WordPress stood out because it was relatively easy to set up, flexible, and could grow with a business over time. The plugin ecosystem made it possible to add functionality without rebuilding sites from scratch. I’ve been using WordPress continuously since then, and it’s still the platform we rely on today for most client websites.

What motivated you to start your own business, and what keeps you going when things get tough?

I spent my first eight years working for a web design and hosting company that ran its own servers in-house. Over time, the person responsible for managing them shifted careers, and the servers were essentially left unattended.

They started going down, regularly, and I found myself spending entire weekends manually restoring hundreds of websites in Microsoft Management Console. There were no backups, no monitoring, and I didn’t yet have formal server management experience. Multiple days of downtime didn’t align with my values around reliability and customer service.

That’s what finally pushed me to start my own company. Like most web designers, I wanted hosting that just worked. I didn’t want to spend my time dealing with servers or fixing preventable problems. 

I initially placed clients on a reseller hosting account, but as the business grew, I moved to a VPS and eventually to a dedicated server to improve reliability and performance. Today, we host a wide range of clients, including offering reseller accounts for other web designers and supporting sites that aren’t built on WordPress.

What’s a hard lesson you learned running your business that’s changed the way you operate?

Staying busy isn’t the same as being productive. Early on, (and for far too long!) I’d open my inbox first thing every morning and start reacting to client emails. If I do that the entire day will quickly disappear and nothing on my “to-do” list gets done.

I learned that without intentional planning, there will always be one more message or urgent request. Once I started setting priorities and carving out time for longer-term planning, everything changed. We became more efficient, made better decisions, and actually got more done in less time.

What’s the best piece of advice you’ve ever gotten and how has it affected your business?

“Raise your prices!” I first heard this in 2006 during a real estate investment class at a community college, and immediately started thinking about how it applied to my web design business. I realized that if I didn’t adjust pricing regularly, I was effectively lowering my prices over time due to inflation.

As your skills improve and the value you provide increases, your pricing needs to reflect that. Last year, we upgraded our server and restructured our hosting plans to include additional features, and raised prices accordingly. That resulted in roughly $30k in additional annual recurring revenue. 

While price increases can feel risky, I’ve found that the number of customers who leave because of them is usually very small compared to the long-term gains.